


The 5 Misadventures of Jessica Drew (+1 Adventure)

by imel



Category: Marvel Cinematic Universe RPF, Real Person Fiction, Spider-Man (Tom Holland Movies), tom holland - Fandom
Genre: F/M, Face-Fucking, Oral Sex, Vaginal Fingering, Vaginal Sex
Language: English
Status: Completed
Published: 2019-09-01
Updated: 2019-09-01
Packaged: 2020-10-04 19:56:56
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,042
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20476655
Author URL: https://archiveofourown.org/users/imel/pseuds/imel
Summary: When you meet Tom Holland, you have the worst luck on what’s supposed to be your best day ever.





	The 5 Misadventures of Jessica Drew (+1 Adventure)

**Misadventure #1: Slice of Life**

It was starting to sink in that you were about to meet Tom Holland for the first time, and you had no idea what you were going to say or do. Most likely act like a lovestruck idiot, but he was probably used to that.

You were wearing your Spider-woman cosplay for the event, and it definitely accentuated your best assets. There was no shame in wanting to look good for your biggest crush.

When you finally approached him, you nervously handed your photo to him to get your autograph.

“It’s the lovely Jessica Drew!”

You were a bit surprised he knew the identity behind your Spider-woman cosplay.

“And the even lovelier Peter Parker!” And god, was he ever lovely. The videos you’d seen did not do the man justice.

“The British Peter Parker and American Jessica Drew,” he mused.

“But you’re a whole lot better at faking it than I am,” you commented.

He chuckled. “I’m sure you’re not that bad.”

“I can assure you that I’m bloody rubbish at it, darling,” you couldn’t help but say in your best, but you knew still godawful, British accent.

You hadn’t really planned on embarrassing yourself, but this whole thing wasn’t going exactly how you’d envisioned it.

He laughed brightly, though, and that was worth it. You could watch and listen to him laugh all day.

“Maybe you are, but I’m sure you have other talents,” he teased.

“I might have some hidden up my sleeve,” you commented, mysteriously.

You watched as he made eye contact with you with those gorgeous brown eyes, your heart thumping faster in your chest. He flipped the photo over to quickly write something down on the back before he handed it back to you.

“Shit!” You hissed as the photo sliced into your thumb.

“Are you alright?” he asked.

“Just a papercut. I’ll survive! Anyway, thanks!” you told him.

“Any time, darling,” he said, smiling at you.

You smiled back and walked away. He even called you ‘darling.’ You were on cloud nine, and very curious what he’d written on the back.

You took a deep breath and flipped it over to find a hotel name, room number and 8pm.

Was he propositioning you? Why else would someone invite you to a hotel room in the evening?

There had to be other possibilities that weren’t just you being overly optimistic, right?

You weren’t sure what to think.

**Misadventure #2: Lovestruck**

You immediately headed back to your own hotel room to change into something that wasn’t your Spider-woman cosplay.

After contemplating your sadly limited options, you decided on a floral blouse and a pair of leggings. You wanted something cute, but casual.

Erring on the side of optimistic caution, you stopped by a pharmacy to grab a box of condoms to put in your handbag.

No matter how much you wanted him, and that was most definitely a lot, you didn’t want to leave with anything that you hadn’t come with.

Then, you headed to his hotel so you’d arrive about 10 minutes early. You made your way slowly down the halls to the room number he’d given you and waited outside the door.

After your phone reached 8:00, you nervously knocked and waited, bouncing on the balls of your feet. You knocked again a few minutes later. No answer.

You played on your phone for a while, taking up some time. Maybe he’d been in the shower and hadn’t heard you.

With one last knock when it hit 8:30, you sighed and walked toward the elevators, shoulders slumped and feeling down.

It was apparently too good to be true.

When you were about to turn the corner, someone ran into you and knocked you to the floor, pain blossoming across your cheek.

“Fuckin’ hell, I’m so sorry,” you heard a male British accent tell you, and it couldn’t be?

You looked up, and it was Tom. You hadn’t been stood up.

“Jessica Drew!” he said in recognition until he saw the bruise blooming on your cheek. “Oh my god, I just assaulted you. Shit, are you alright?”

You fell into a fit of giggles at how ridiculous this was.

“Stop laughing at me!” he complained, but started laughing himself.

“Don’t worry, I’m fine,” you eventually told him.

“I was running late, and I was in a rush to get back here to see you before you left thinking I was a dick,” he explained.

“That’s really sweet of you,” you said. “You caught me just in time. I was about to leave.”

“Let me go grab you some ice, and we can head back to my room,” he suggested.

**Misadventure #3: I’ve Got My Eye On You**

You waited inside Tom’s room while he went to get you some ice for your cheek, going to the bathroom to check your face in the mirror.

It was definitely going to bruise, but you honestly didn’t mind. Spending time with him was entirely worth a bruise.

The door opened, and Tom returned, coming into the bathroom to grab a washcloth to wrap the ice in. He handed it to you.

You placed it against your cheek, hissing at the soreness of the contact and cold.

“I’m so sorry, darling,” he told you, guilt apparent across his face.

“I’m okay,” you reassured him.

“Let me show you a good time to make up for it?” he asked.

Your heart started pounding in your chest. You swallowed. “What did you have in mind?”

“I invited you to my hotel room. What do you think?” he teased, eyes glinting mischievously.

“I don’t know. Maybe some Bible study?” you joked.

“Well, I’m definitely hoping to hear at least a few ‘oh god’s by the time tonight’s over.” He ran a finger down your arm, leaving goosebumps in its trail.

You gasped. So, he was propositioning you. That was something you could definitely get on board with. A bruise and a papercut were so worth this.

He took the ice from your hand and placed it on the vanity. “Is it alright if I kiss you, sweetheart?”

You nodded, probably too eagerly, but you couldn’t bring yourself to care. Tom fucking Holland wanted to kiss you.

“Come on,” he said, taking you by the hand to lead you to sit on the edge of the bed with him.

You turned to look at his handsome face, your eyes meeting his. Instead of waiting for him to close the gap, you kissed him, shutting your eyes when your lips pressed together.

From there, he took the lead.

His tongue made its way past your parted lips and ran across your teeth. You let him in and brushed your tongue against his, exploring each other’s mouths.

The kiss turned from unhurried to heated rather quickly, one of his hands cupping your breast through your top while the other slipped under the hem of your top to brush against the bare small of your back.

You moved down onto your knees in front of him, pushing his legs apart to make space for you between them. You popped the button on his pants and pulled down the zipper, eagerly freeing his erection from the confines of his boxers. 

He was slightly above average in size with a nice curve that you already knew would hit your g-spot just right when he fucked you. And god, he was going to fuck you. Maybe even more than once. Your life was awesome. 

You wrapped your hand around the base and took the head in your mouth, swirling your tongue around it. His precum was bitter on your tongue, but you didn’t mind. You took him as deep as you could, gagging slightly. 

He moaned when you did that. You took his hand and put it on the back of your head. 

"Want me to fuck your mouth, love?" he asked. 

You nodded vigorously. 

"Whatever the lady wants," he agreed. 

You let go of his dick with your hand and let him take over.

He tangled his fingers in your hair and started tentatively thrusting into your mouth, gradually going deeper and faster.

You noticed he seemed to enjoy it the most when you gagged slightly, so you encouraged him to do that, to take what he wanted.

It wasn't long before he pulled out of your mouth and began cumming on your face in spurts, while you watched his face as he climaxed, rapt. You’d always wanted to see him fall apart like that, and it didn’t disappoint.

You realized too late that you'd made a mistake. His cum got in your eye, and dammit, that burned. Involuntary tears streamed down your face at the sting. 

"Are you alright?" he asked, after he glanced down at you, concern apparent across his face. "Did I accidentally touch your cheek?" 

"No, just got cum in my eye. I should have closed them, but I wanted to watch you," you admitted.

"Oh, darling," he said, pulling you into a hug. "You're not having the best luck today, are you?" 

"Well, I am here with you. I assure you that's entirely worth the little mishaps." 

He chuckled. "Let me take care of you now and make it even better."

**Misadventure #4: A Breath of Fresh Air**

Tom retrieved a damp washcloth from the bathroom and gently wiped your face clean while you sat on the edge of the bed again, careful with your cheek.

“There, that’s better,” he said after he was finished. 

“Can I take these off?” he asked, playing with the hem of your top.

“Definitely,” you replied.

He undressed you unhurriedly, fingers brushing teasingly against the newly bare skin.

When you were finally naked, he quickly took off his own clothes, not making a show of it. 

You were glad because you wanted him badly, and you weren’t in the mood to wait.

“Now, lie down, and I’ll make you feel good,” he told you.

You didn’t have to be told twice, lying down at the top of the bed. He joined you.

His lips were soon back on yours while he palmed one of your breasts, toying with your already hardened nipple.

The feeling went straight to your core, and you rubbed your thighs together automatically.

You broke the kiss. “Please,” you begged against his lips.

“Do you want my mouth or my hand first?” he asked quietly.

“Would you talk dirty to me if I picked your hand?” you requested.

“I can do that,” he agreed.

You spread your legs while his hand slid down your stomach to brush over your mons. His fingers slipped between your folds, and you whimpered.

“Eager, aren’t we?” he commented. “You’re fucking soaked, too. Did sucking me off really turn you on that much?”

“Yeah,” you confirmed. “I’m not sure if you’ve noticed, but you’re extremely hot.”

He chuckled. “I might have been told that a time or two, yeah. You’re still talking in complete sentences, though. We definitely can’t have that.”

You moaned when he pushed two fingers inside you while his thumb found your clit, rubbing slow circles around it while he moved his fingers in and out.

“Nice and tight for me, too. You’re going to feel like heaven around my dick. I’ll fuck you into the mattress, until you forget everything but my name. Would you like that, love?”

“Yeah,” you told him, a bit breathlessly. “Please.”

“Nope, you don’t get my dick until you cum for me first.”

“Can you faster?” you whined.

“You’ll take what I give you,” he said, but his thumb sped up a bit regardless, and he pressed a third finger into you.

His fingers curved up to brush against your g-spot every few thrusts, and it felt amazing. No one had ever made you feel this good before, and he was just using his hand to pleasure you. You hadn’t even had his mouth or his dick yet.

“God, Tom,” you moaned, grabbing his free hand and interlacing your fingers with his.

“Love the way you say my name, sweetheart, “ he commented. “Are you going to cum on my fingers?”

“Almost there, Tom,” you said, wanting to please him.

Your orgasm hit you, and it was intense. You called out his name repeatedly.

He fucked you roughly with his fingers, and the worst possible thing you could think of at the moment happened. You farted, loudly and unmistakably.

You immediately let go of his hand and covered your face with both of your hands. Your hand pressed against your wounded cheek, making you cry out in pain.

You could tell he tried to suppress it, but he started laughing and couldn’t seem to stop.

“I’m so sorry,” you groaned, hiding your face still. “I can leave if you want me to.”

“I don’t want you to go anywhere. Really, don’t worry about it. It happens,” he eventually said after he calmed down.

“I’m so embarrassed,” you told him.

He moved your hands away from your face and kissed you lightly.

“You still want to keep going?” you asked.

“Only if you do,” he responded.

“Yeah, I do,” you said.

You were pretty sure you’d regret it for the rest of your life if you didn’t actually have sex with him, bad luck be damned.

**Misadventure #5: Ride ‘Em Cowgirl**

“I’ll be right back.” You went over to your purse to grab a strip of condoms.

“I think you have more faith in my stamina than I do,” he said, chuckling.

“Just being prepared in case.” You tore one off the strip and rolled it down his erection. “Can I ride you?”

He nodded. “Be my guest.”

You climbed on top of him and positioned him against your entrance, then slowly sank down until your bodies were flush. You paused to adjust. “God, Tom, you’re so big inside me.”

“You’re fucking tight and hot. I can tell you’re wet, too. Wish I could feel it,” he commented.

“With the luck I’m having today, we’d somehow both end up with gonoherpasyphilaids, and a baby in 9 months.” You were only half-joking.

He laughed. “I wasn’t suggesting barebacking. It’s important to be safe.”

You started moving your hips up and down unhurriedly, enjoying the feeling of him brushing your g-spot as you moved.

After letting you set the pace for a while, he started thrusting up into you faster, grabbing your hips to pull you down harder.

You head dropped back as you loudly moaned, meeting his thrusts.

“God, I’m getting close,” you told him.

His fingers moved up to find your clit, collecting some of your wetness before rubbing it with a single fingertip, fucking you faster and harder.

You quickly climaxed again, all uninterrupted pleasure this time, toes curling and nails digging into his skin. It was everything you’d hoped the first orgasm you’d had with him would be.

“Stop, too much,” you told him after you came down, and he stilled.

“Can we try reverse cowgirl now?” he asked, breathing a bit hard.

“Yeah,” you agreed.

You started to crawl around to face away from him and fell off the bed instead, your side thudding very painfully on the hard floor.

“Fuck, are you alright?” he asked.

“This is the worst best day ever,” you groaned into the floor.

He climbed down next to you and helped you to your feet again. 

You hissed in pain, tears dripping down your cheeks, when he grabbed your left wrist.

“Let me see,” he said, looking at your wrist. “I hate to tell you this, darling, but I think it’s broken. Do you want me to take you to the hospital?”

You sighed, sniffling. “Not really, but do I have much of a choice?”

“No,” he told you. “I’m going to have to insist. I couldn’t in good conscience let you leave without making sure you get it looked at.”

“If you’re not busy, can I have a do over at some point tomorrow? The fucking me into the mattress thing? I want that.”

“Absolutely,” he agreed. “I don’t want you to remember me as the worst sex you’ve ever had.”

**Adventure #1: A Do-Over**

The hospital wasn’t fun, but Tom remained by your side the entire time, and was even sweeter than you’d imagined him being.

Now, it was time for your do-over.

Your wrist, in its new cast, was carefully placed above your head out of immediate reach as Tom positioned himself on top of you, at the center of the bed where you were unlikely to fall off.

He positioned himself at your entrance and pushed in slowly until he bottomed out, eyes focused on your face.

“Feeling alright?” he asked.

“I’m good,” you replied, “but I’d be better if you moved.”

His thrusts went from slow and gentle to quick and rough in increments, fueled by the noises you were making and desperate pleas.

“I’m so close.” You reached your free hand down between your bodies to get yourself the rest of the way there. He moved it away and used his own fingers to rub your clit in small circles to the pace of his thrusts.

“Tom, I’m going to-” Your climax hit you hard, pleasure coursing through your entire body from head to toes. You cried out his name between moans.

He plowed into you, chasing his own orgasm. With a last few erratic thrusts, he spilled into the condom, your name on his lips.

Once you had both come down from your highs, he carefully withdrew and walked over to the bathroom to get rid of the condom.

“Do you cuddle?” you asked hopefully as he returned.

“I love to cuddle,” he said, lying back down and tugging you close to him, careful of your arm.

“Thank you for the do-over,” you told him. “That was what I’d been hoping for.”

“You know, I still haven’t eaten you out,” he pointed out. “I wouldn’t want to deny you the full experience.”

“Do we have time?” you asked.

“I don’t fly out until tomorrow night,” he replied. “We have plenty of time for me to see how much I can make you cum in 36 hours.”

You grinned. “Sounds like a plan.”


End file.
